I have two fretless basses. One has roundwounds for that 'electric' fretless sound you mention. The other has tape-wound Labella strings for a fatter, more DB sound. I'd suggest you try using a chorus if using roundwounds (chorus AND octaver can sound great.)
your ebony board will show signs of wear, but find yourself a good local luthier -Martin at the Bass Gallery - and they'll be able to advise what needs done, and when. Good luck in your adventure(s).